Sara Schaefer on Coming Out of Her Chrysalis

Sara Schaefer has proven herself as a capable and talented comedian on nearly every front in comedy. Together with Nikki Glaser, she hosted Nikki & Sara Live on MTV, was the head blogger for Late Night with Jimmy Fallon (for which she won the Emmy Award for Creative Achievement in Interactive Media), ran a successful three-year podcast, You Had to Be There, with Nikki Glaser, and has been producing a great new podcast, LIES, through Nerdist and WNYC.

All the while, between the jobs mentioned above and also working as a financial analyst at various law firms, Schaefer has been developing her standup. Her debut album, Chrysalis, is a tribute to her development as a comedian. On the album, she balances between witty observationalist humor and skillfully detailed stories about sensitive moments in her development. Though it’s been long in waiting, Schaefer tells us that we can expect to see more of her standup in the years to come.

I was glad to have a conversation with her over the phone about all this, as well as how she’s adjusted to her new home in LA, whether she feels more creative when happy or depressed, and what she hopes to achieve in the long-term.

So you’ve already done a pretty wide variety of things in your career so far; what inspired you to do your album now?

Yeah, I realized I’m known for different things, and this whole time I’ve been doing standup, and that’s been the through-line of everything, and I’m not as well known for that. I wanted to put something out there to show, “Hey, I have this body of work that I’ve been working on.” Also, I haven’t done a Comedy Central Half Hour, I’ve never done a set on a late night show, I’ve only done standup on TV once. My standup isn’t very available; I don’t put a lot of videos of it online because I’m super picky.

You definitely chose some great material to put on there; I loved it.

Thank you so much! I just feel like I was ready and it was time to lay some of this down, some of this material, and feel a little free to move on and go on to the next phase of my material.

Isn’t that also a little nerve-wracking? It’s all great material, but I imagine there this feeling of saying farewell to these bits that you love so much.

Yeah, I dealt with that and struggled with it for a little bit. Being on the road lately and being at festivals especially, you’re doing this showcase set for fifteen minutes, and you’re trying to make a good impression and put your best foot forward. Some of these jokes are like my crutch, “Oh, this is how I get the audience on board right away.” But I’m getting sort of tired of doing them, so I’m like, “What’s my new crowd-pleaser? What’s the new thing?” Then you always do the old jokes. There’s no rules, but there’s a love-hate feeling in letting go of these jokes. The new stuff, it hasn’t been tested the way these others have.

Does that feel like you’re resetting yourself or something like that?

Yeah, I’m still trying to get a set on a late night show, and I think that’s going to happen soon. I have a good feeling about it. Some of those things I’m reserving. I’ll do some of these older jokes, but I’m really excited about leaving some of this stuff behind and relaxing a little. Because when I first started out, I was doing really different stuff. I was doing songs, I was doing multimedia type stuff; a lot of it was because I didn’t know what else to do. I was afraid to just talk on stage. Now, maybe I can relax a little and try different things and expand past what I’ve been doing for the past ten years, I guess more like five or six years. Just explore and try new things.

I notice that among the jokes on your album you have a mix of very standard, observational humor, like your opener, and then you go into more story-ish jokes. Do you feel more comfortable in one realm than the other?

I actually feel more comfortable in the story-telling realm. I was doing that a lot when I first started telling jokes. Writing a joke, a classic joke, a structured joke is still something that I’m like, “How do you do that?” That part was really hard for me. A lot of those more observational jokes came from a desire to get my standup on TV, to showcase things. Because when you do a showcase, whether it’s for a festival or anything, they want you to do these really quick jokes that are topical and easy to understand and all that stuff. I forced myself to try and figure that out and I’m glad I did, and now I know how to do that, but I’m definitely looking forward to getting into more of the stories. Now that I’m able to headline I can really explore those things in a way that I wouldn’t be able to before.

So does that mean you’re going to pour more of your energy going forward into your standup, or are you also developing other projects? Like you have your great new podcast LIES.

I’m always trying to do everything I can all at once, but the standup has been something I’ve been focused on the last year especially, because I haven’t had a big day job, so I’m able to really focus on the standup. Knowing I wanted to do this album, I really worked hard on my jokes and made sure I was getting on the road enough to get ready. I’m still kind of in that zone. I have a lot of new ideas that I want to work on in my standup. I want to get more personal. A lot of my stuff, to me, is very personal, very intimate. I want to do things with the audience, like “I know who this person is”, and then maybe I can figure out who I am.

With my other projects, the podcast is on hold right now because we’re waiting to see what WNYC wants to do. They’re big public radio, so they kind of move slow, which is fine, but I would love to keep doing that. I’m developing a couple of TV shows right now, those are a lot of waiting, this process is very slow. Once those things go forward, I’m probably going to be really busy. When I was doing Nikki & Sara I didn’t do much standup at all. I know once I get something that’s more of a daytime job, and I’m focused on that thing, the standup will probably take a back seat for a while. That’s been one of the amazing things about the past year. I had this TV show, it consumed my life for a couple of years, and then went away and I had all this time on my hands. Some of it was just me not knowing what to do and being frozen and depressed and stuff.

It reminded me that I’ve been doing something this whole time that’s like a well I can go back to. That’s standup. Standup is a well you can always go back to. You have a body of work that doesn’t go away, it doesn’t disappear. You have experience that doesn’t go away. Yeah, you might be rusty, you might need to get back out there and build up those muscles again but you don’t forget everything. In that sense, if my career took me in a direction where I didn’t have as much time for standup, I’d be okay with that, but I don’t think I’d ever want to let go of it completely.

To that end, how do you find yourself ‘building up those muscles again?’ Do you still go to open mics?

I was not a huge open mic person to begin with. I stopped going to open mics pretty early on because they made me really sad. I wasn’t getting a lot out of it. I wouldn’t get the laughs. It’s hard to get laughs at an open mic. And people will say, “If you make the comics laugh, then you know it’s funny.” Not necessarily. That may be something that only comics think is funny. I did a couple in LA that were sort of hybrid, where some people are actually booked. I actually really enjoyed it because I saw a lot of comedians I’ve never seen before, and I’m seeing people try things out. I was like “Oh, I can just go up there and just say whatever I want, and there’s no pressure.” I forgot about that no pressure feeling.

After being a comedian in New York for so long, how do you feel that the move from NYC to LA has affected you?

A lot of my friends are out here and there’s a lot of really great shows. It’s definitely a different vibe. I feel like, in LA, it’s weird, I didn’t expect this, but you can do really weird stuff in LA and the audience really likes it. You can be kooky and you can do something more performance-artsy, and people embrace that more in LA. Maybe because LA people are psycho, I don’t know. Everybody’s weird and out here, but in New York, I feel like people, if you do something that’s too “out there,” people are just like “What are you doing? I don’t have time for this.”

New Yorkers pull back more easily.

Yes, that’s exactly the thing. Also in LA there are a lot of shows … It was nice to move to a city, I’ve been established enough where, although I definitely still have to ask to get booked on shows—people aren’t like knocking my door down to perform—but I just find out where the shows are and I’ve been able to get booked pretty easily on most things. And that’s been really great, because there were times in New York I’m like, “Does anybody even know who I am?” In LA, you just get out there and go to different shows.

One thing in LA that I find that I’ve discovered that’s a new thing for me is what I call “backyard shows.” People put on shows in their backyard. It’s like everybody has a backyard or outdoor space in LA and the weather’s always good, so you can have an outdoor show. I have to say no to them now because I get so much anxiety about there being a show in someone’s backyard. I’m worrying the entire time that some neighbors are going to get mad. That’s literally what’s going through my head, and I can’t perform. I’m being quiet, I’m not doing my jokes the way I normally would. I’m like, “What if a kid is listening, and I say the F word?” I can’t do it, and they’re cool shows and stuff, but I’m just like “No.” I’m too uncomfortable. I can’t even enjoy watching it. I’ve done like three of them, and after the third one, I’m like, “those are not good for me. I probably should just say no to them.”

There have to be so many more distractions for the audience.

Yeah, I did one, and there was like a pitbull on the other side of the fence like barking at me, and I’m just like, “Oh my god! I’m going to get killed here.” It’s interesting. It depends on the show, you know? Most of them I’m just too … Everyone else is having a great time, everybody else is enjoying it. These are great shows, but I’m like “No!”

Have you found that the nicer weather and brighter disposition of the locals has changed your comedy at all?

I mean for one thing, I’m just happier here. Overall, my life is more comfortable, and I find myself observing more. I’m outside. Yes, there’s a difference in observation, there’s a different level of things you’re noticing in the world. I actually like it because it’s a little more like the rest of the country. Our culture is what most people live in. Going to Target is the same in LA as it is in the rest of the country, but in New York, everything is different.

I came up in comedy in New York and I wasn’t on the road, so I did have a limited point of view of what life is. You see that sometimes in New York; comedians are doing jokes that are like, “Oh, all you have is New York material”. When you go out on the road, you have to see if anybody can understand that, if they can relate to it. So I think being on the road a lot in the past few years has helped me break out of that a little and made sure I’m not doing that.

Do you find that being happier with where you’re living and what you’re doing, do you think that helps you produce better material, or do you subscribe more to the idea that suffering helps with material and so forth?

I’ve actually gone back and forth with that. I actually had a pretty tough year last year. I was depressed for a little while. The first six months I was in LA I was happier in many ways, but I was also depressed in other ways. It was a weird thing happening. I don’t know what it is exactly.

But still overall, I was definitely more relaxed in LA. I do think being happier, I’m more creative when I’m happier. When I’m balanced and sleeping well and feeling good, those things. I feel more creative because I’m feeling more confident, and I’m feeling motivated and I have energy.

But at the same time, when I went through my divorce it was the hardest time in my life. It was a major turning point in my standup because I basically went from—It wasn’t because I was depressed and suffering. I was having a completely new experience in my life. I was looking at things from a different point of view. I was taking risks that I wouldn’t have taken before. I was living more of a present life, because I was being pressed into a walk of life that I didn’t understand, and I was going through a major change. So in that way, even though it was suffering, the good material that came out of it was more from the positive aspects of that. It’s a weird juxtaposition of how that works.

What I’ve come to learn now is that a lot of my material comes from realizing that a really mundane story that I’ve been telling my friends and family for a while is interesting, like “Oh, that could be a joke. What if I just told it on stage see what gets laughs and see how it goes?” These thoughts I’ve had have been rolling around in my head and we’ll see how that goes. That’s why I named the album Chrysalis. There’s multiple reasons, but one of them is because I feel like this material represents me developing as a comedian. That this is a representation of me in that cocoon, and now I’m a beautiful butterfly. I don’t know if I am, but I’m hoping. I’m visualizing that.

What’s do you have in mind primarily for yourself in the future? What would you like to develop into, ideally?

The two ideas I’ve been working on I can’t really talk about, but one is more of a scripted idea. One would fall more in a more satire sketch idea. They’re both—there’s movement, there’s things happening. One will become a pilot at least, which is really exciting. It’s taken a long time to build those blocks and develop those ideas. I really want to do another show that I create and whether I’m the star of it or not, I just want a sense of the ideas. Trading ideas and seeing it come to fruition.

Ultimately, I think, what’s really exciting to me right now in long term plans is I would love to have a production company that—I mean, I have one, but to have it grow and become an actual company that’s producing things and making things whether I’m in it or not. For someone to be like, “You have offices and employees!” I’m thinking of those things long term, and it’s smiles and a goal.

Photo by Mindy Tucker.

Phil Stamato lives and writes in New York, where he may also be seen standing up and telling jokes.

Sara Schaefer on Coming Out of Her Chrysalis